


Dressed For Success

by flipmeforward (vinterdrog)



Category: Glee
Genre: Boypussy, Boypussy Kurt, Crossdressing Kink, Fingerfucking, M/M, Penis In Vagina Sex
Language: English
Status: Completed
Published: 2014-08-24
Updated: 2014-08-24
Packaged: 2018-02-14 12:08:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,371
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2191293
Author URL: https://archiveofourown.org/users/vinterdrog/pseuds/flipmeforward
Summary: <blockquote class="userstuff">
              <p>When Elliott comes out in the living room, Kurt is sitting on the floor by the coffee table, Elliott’s computer open in front of him, and with an expression Elliott can’t quite parse. Then Kurt looks up at him, and Elliott is reminded with startling clarity just what he was doing before he went to make tea. </p>
<p>He was browsing for porn. </p>
<p><em>Kinky</em> porn.</p>
            </blockquote>





	Dressed For Success

It’s one of those days where they just pass by each other all day. Elliott kissing Kurt goodbye on his way out of the door, while Kurt is just entering the kitchen to have breakfast; a couple of quick text messages when Kurt’s lunch break ends, just as Elliott’s begins; a five-minute conversation in the hallway when Elliott comes home and Kurt is leaving for his shift at the diner. 

When Kurt gets home again it’s pretty late, but it’s a Friday, and they’re both free the next day. 

“Hey,” Elliott says, smiling warmly when Kurt joins him in the kitchen. “How are you?” He turns away from the counter and the tea he’s making, opening up his arms for Kurt, who goes straight into his embrace. 

“Tired,” Kurt says, his voice muffled by Elliott’s t-shirt. “ _So_  tired.”

Elliott kisses his temple and strokes his back. “You’ve had dinner?” Kurt nods. “You want tea?” Another nod. “My computer’s on the coffee table, go put on a movie and I’ll be right there, okay?”

“I love you,” Kurt says, leaning up to press a kiss to Elliott’s jaw, before he does as he’s told. 

When Elliott comes out in the living room, Kurt is sitting on the floor by the coffee table, Elliott’s computer open in front of him, and with an expression Elliott can’t quite parse. Then Kurt looks up at him, and Elliott is reminded with startling clarity just what he was doing before he went to make tea. 

He was browsing for porn. 

_Kinky_  porn. 

Not that his and Kurt’s sex life is particularly vanilla, but they’ve never done…this. 

“Do you have something you need to tell me?” Kurt asks, his voice just as unreadable as his face, and it makes Elliott nervous. He doesn’t know what to say, doesn’t know  _how_  he should say it, because he has no idea what Kurt is thinking right now. 

“I—uhm,” he says, falters. Kurt knows that Elliott watches porn sometimes, so it’s not that. It’s most definitely the nature of the porn. 

Amateur videos of guys masturbating…while wearing skirts, or panties, or sometimes both. It’s not a new thing for Elliott, far from it, but he hasn’t known how to bring it up to Kurt, and he hasn’t particularly felt like he  _needs_  to. Kurt has told him about high school, and for Elliott, seeking out the porn once every other month has been enough. 

Kurt’s arched eyebrow reminds Elliott that he’s still waiting for an answer, so Elliott sits down on the couch and puts the mugs on the table. 

“I’m sorry I didn’t tell you,” Elliott says finally, because he is, kind of, and it’s the only apology he can give without lying. He’s not sorry he was browsing for porn, he’s not sorry he was browsing for that particular kind of porn either, but he still feels like he should apologize. 

“Why didn’t you?” Kurt says, his voice a little softer, and Elliott tries to not breathe out a too-loud sigh of relief that his boyfriend isn’t mad or upset. 

Elliott shrugs. “I wasn’t sure you’d be comfortable with it. And it’s not that big of a deal to me, so. It didn’t matter. It  _doesn’t_  matter,” he adds, not wanting to pressure Kurt into anything. 

Kurt looks silently between Elliott and the screen a couple of times. “Okay,” he says eventually, then clicks around on the computer before plugging in the hdmi cable and pulling himself up to sit on the couch. Their Netflix queue starts playing and Kurt leans back, shifting closer to Elliott, who doesn’t dare to relax until Kurt has been silent for ten minutes. 

Kurt doesn’t say anything else about it over the next few days, and Elliott does his best to put it out of his mind. He manages it well enough that he gets completely surprised when he gets home a couple of weeks later. He knows Kurt is home, they texted just half an hour earlier, but there’s no sign of him in neither the kitchen area nor the living room. 

“Kurt?” he calls, dropping his bag and taking off his jacket. 

“In here,” comes the reply from the bedroom, which—what? It’s barely eight pm yet. 

“What’s the matter?” Elliott asks, making his way. “Are you sick? Are—” he stops short when he gets to the doorway and sees Kurt. 

His boyfriend, his  _insanely hot_  boyfriend, is sitting on their bed, his legs crossed, wearing a tight, short-sleeved shirt and…a skirt. It’s a pleated, dark gray thing, neatly arranged over his thighs, stopping just above his knees. Just under the knees he’s wearing black socks. 

“Hi,” Kurt says, uncrossing and re-crossing his legs. Elliott catches a glimpse of something red, something that didn’t look like plain cotton, and he swears he can  _feel_  all the blood in his body rushing to his cock. 

“What…what is happening?” Elliott asks, feeling behind him for the doorframe. He’s lightheaded, he needs to hold onto something to not fall over. 

A flash of uncertainty passes over Kurt’s face, and he shifts a little. “I—you don’t like it? I thought you’d—” He cuts himself off, biting his lip. It takes Elliott a second to realize what he just said, but when he does, he crosses the floor and falls to his knees in front of Kurt, puts his hands on Kurt’s knees, makes him uncross them, and looks up at him. 

“Sweetheart,” he says, trying to keep his voice as steady as possible while his body is thrumming with arousal. “I  _love_  it. I—god, you’re  _so hot_ , I’m—” He rubs his thumbs on the inside of Kurt’s knees, between the skirt and the socks. “I honestly can’t decide if I want to tear all your clothes off and fuck you senseless, or just make you lie down while I jerk off and watch you,” he says, reaching down to squeeze his cock. “This is— _so hot_.” Elliott hopes Kurt understands how much he actually means it, despite being so turned on that his voice is shaking. 

“Yeah?” Kurt says, gaining confidence again and spreading his legs. Elliott gets a better look at his underwear now; he was right, they’re not plain cotton — they’re red lace. 

“ _God_ ,” Elliott breathes out, sliding his hands further up Kurt’s thighs, in under the skirt. He rubs his thumbs against the edge of the panties, smiles when he hears Kurt’s breaths stutter. “You like this, too?” he asks, really hoping for an affirmative answer, because he  _needs_  to see Kurt like this. He didn’t know he wanted it this bad, but now that he has it, he’s not sure he’ll be able to go without it. 

“Yes,” Kurt says on an exhale, his face turning red with embarrassment as well as arousal. “I didn’t—I didn’t know I would, but I do.” He spreads his legs even more, scoots down a little on the bed, basically inviting Elliott in between his knees. Elliott reaches out, strokes his thumb against the outline of Kurt’s pussy, feels how damp he is already. 

Kurt moans and Elliott can’t hold back a groan, leans in and puts his mouth on Kurt, over his underwear. Kurt leans back, reaches out a hand to tangle in Elliott’s hair, trying to spur him on. Elliott doesn’t budge, though, just keeps mouthing lightly, inhaling his scent and getting his underwear wet, before he sits back again. He pulls both of his shirts off over his head in one move, then stands up to make quick work of his pants. Kurt is eyeing him hungrily the whole time, leaning back on his elbows and licking his lips. 

“Are you gonna fuck me?” he asks, back to his more confident self now, when he knows his plan worked. He raises one leg up on the bed, making a truly obscene picture with his skirt splayed around him and his wet panties clinging to his pussy. 

“Later,” Elliott says, stepping out of his own underwear and climbing onto the bed. He leans down and kisses Kurt, deep and dirty from the start, swallowing Kurt’s pleased moans. 

“So what  _are_  you gonna do?” Kurt asks when they break apart. Elliott looks at him, admires his kiss-swollen lips and can’t help but be amazed, once again, at how easily Kurt just gives himself over, trusts that Elliott will take control over everything and lead them both in the right direction. 

“I’m gonna finger you,” he says after a too-long pause, but Kurt doesn’t seem to mind, or even care. “Come here.” Elliott sits back on his heels and taps his thigh, motioning for Kurt to straddle it. Kurt does, easily, arranges himself comfortably and puts his arms around Elliott’s neck, holding himself close. Elliott wraps one arm around Kurt’s waist, puts the other hand on Kurt’s thigh and strokes it in broad, firm strokes, getting closer to the hem of Kurt’s panties with every move. 

“I’m gonna fuck my fingers into your pussy,” Elliott says into Kurt’s ear, his warm breath ghosting over Kurt’s skin making him shiver. “I want you to ride my hand and come all over your panties and my leg, can you do that?”

Kurt whines into Elliott’s neck and trusts forward, trying to get Elliott’s fingers where he wants them. “These are Calvin Klein,” he protests, but there’s no actual objection in his voice. 

“I’ll buy you more,” Elliott promises quickly and finally moves his hand to rub at Kurt’s pussy. “I’ll buy you a lot more.” He strokes the lace, presses it into Kurt’s lips, uses the whole length of his hand to press against as much of Kurt’s pussy as he can cover. “You didn’t answer my question,” he reminds when Kurt whines again and tries to push against Elliott’s hand. 

“Will you fuck me after?” Kurt asks. “I really—” Elliott slips one finger inside the panties and Kurt gasps. “— _Really_  want your cock inside me,” he finishes breathlessly, jerking against Elliott’s fingers, trying to get  _more_. 

“Sure, baby,” Elliott agrees. “Just do this for me and I’ll fuck you hard, later.”

“I love you,” Kurt murmurs, burrowing his face even more in Elliott’s neck and lifting himself up a little, giving Elliott better access to his cunt. 

Elliott takes the cue and slips another finger inside the panties, pushing them to the side to give himself more room to move. Kurt is slick and swollen and Elliott’s finger slide easily between his lips, nudging against his hole, rubbing his clit. The skirt still covers most of it, so when he looks down he only sees part of his forearm move in and out under the skirt, but somehow, that image is _ridiculously_  hot, almost as hot as watching his fingers slip in and out of Kurt’s pussy, but just almost. He loves watching his fingers or his cock getting swallowed by Kurt’s hole, pushing in and out in a relentless rhythm, making him come over and over again, clenching around Elliott until Elliott can’t stand it anymore and comes, too. 

But, yeah. This is also good. Elliott tightens his grip around Kurt’s waist, keeping him steady while he adds more force to his fingers. They’re both well-built men, but Elliott is still just  _bigger_  than Kurt; he’s taller, broader, his arms are bigger, and they look damn good wrapped tight around Kurt’s slimmer body. 

“Come on, baby,” Elliott coaxes, rubbing his thumb against Kurt’s hard clit. His breathing is hard against Elliott’s shoulder and Elliott knows he’s close, it never takes long to bring him over the edge the first time, so he speeds up the movement of his fingers. The panties are restricting him slightly, but Kurt doesn’t seem to notice, he just rides Elliott’s hand as good as he can while still being gripped tightly. 

“Please,” Kurt whines, “Please, just—” He doesn’t finish, doesn’t need to, Elliott knows what he wants. He presses his nails into the soft flesh of Kurt’s thigh, almost hard enough to draw blood, and then he smacks him right above the crescent-shaped marks, the sound echoing in their bedroom. Kurt makes a sound that gets stuck in his throat, rocking forward onto Elliott’s hand and gripping tighter around his neck, and when Elliott rubs hard over his clit again, he comes, sobbing hard and his body shaking, his pussy clenching around Elliott’s fingers and his knees clutching Elliott’s thigh. 

“Fuck, fuck,  _fuck_ ,” he chants, the word turning into inaudible mumbling as he comes down from his orgasm and the shivers die out.

“ _God_ ,” he says when he’s finally calmed down and sits back on his heels. He winces at the stiffness in his legs and Elliott smiles as he helps him lie down on the bed. “That was good,” Kurt says, reaching up to wrap his arms around Elliott’s neck again and pull him down for a kiss. 

“Yeah?” Elliott says, laying down beside him for a better angle. 

“Mm,” Kurt hums. “Love your arms around me.” He sounds sleepy, but Elliott knows that he’ll get his energy right back as soon as he lets his hands slip below the waist. 

“I love my arms around you, too,” Elliott says, pushing Kurt onto his back and hovering over him, giving him another kiss. “Makes me feel like you belong to me.”

“I do,” Kurt says, like it’s really that easy. He wraps one leg around Elliott’s, forcing him down on top of him. His legs are still clothed, and Elliott’s bare cock rubs against the rough fabric of the skirt when he’s pressed down, but it does nothing to soften his erection. “You want to fuck me, now?” Kurt asks. “While I’m still wearing the skirt?” He shifts a little and arches, making his crotch align with Elliott’s dick through the skirt. “You gonna flip it up and watch us?”

Elliott groans and thrusts down, bending his head to nip at Kurt’s neck. “You’re so fucking filthy,” he growls. “How long have you been planning this? Since you saw that site on my computer? Since before that?” He sits back and slides his hands in under Kurt’s skirt and pulls down the panties, doesn’t care about being gentle. “How long have you been dressed like this today? I bet you touched yourself before I got home, too, you were already wet when I started touching you.” He slides two fingers into Kurt again, twists them and watches Kurt squirm and whimper on the bed. 

“What did you think about? This? Me fingering you? Or me fucking you?” He moves between Kurt’s legs, spreads them. “Did you think about me licking you?” he asks, and bends down to do just that. Kurt moans loudly and Elliott smiles. This is not part of his plan for tonight, but a taste won’t hurt. He licks from Kurt’s asshole to his clit, sucks on it a little and slides his tongue into Kurt’s hole, between his fingers. He makes sure to rub his bearded jaw against Kurt’s swollen pussy lips too, taking great pleasure in watching Kurt shiver and clutch the sheets. They’d discovered that by accident, and it had taken them both by surprise, but they’ve done the most of it since. He licks a couple of more times, then backs off again, sitting back on his heels and stroking his cock. 

“Are you okay?” he asks, nodding towards the bedside table. Kurt reaches down and slides two fingers into himself, letting them linger a little longer than what’s really necessary. 

“Yeah,” he says and nods, pulling his fingers out, but Elliott grabs his wrist before he can wipe them on the sheet. 

“Good,” he says, then sucks Kurt’s fingers clean. He shuffles forward, aligns his cock with Kurt’s pussy, rubs it against him a couple of times. 

“Stop teasing,” Kurt complains, spreading his legs wider and hooking one heel around Elliott’s thigh and pulling him closer. “Just fuck me.”

“Yeah, okay,” Elliott breathes out, then pushes his cock into Kurt. “Okay.” He goes slowly, not because it’s necessary, but because he wants to savor the picture of his naked body against Kurt’s fully clothed; the skirt flipped up over his stomach, the shirtsleeves hugging tight around Kurt’s biceps. Elliott’s hands on Kurt’s hips, holding on, keeping him steady. The tattoos that make a stark contrast to their pale sheets and Kurt’s white shirt, and they just look  _so good_ together; Elliott would’ve been jealous of himself if he was someone else. 

“Come on,  _fuck_  me,” Kurt says, breaking Elliott out of his thoughts. He slides his leg higher up, puts his heel on Elliott’s ass and forces him to push in the last bit. “ _Yes_ , please.”

“Jesus, you’re so hot for it,” Elliott marvels, but obliges and starts to fuck Kurt, hard and fast. The bed squeaks under them and Kurt is shoved further and further up the bed with every thrust, but he doesn’t seem to mind at all. 

“Yes,” he agrees, even though Elliott doesn’t know if he’s sure what he’s agreeing  _to_. “Love your cock.” Then again, on the other hand, he could be _completely_  aware what he’s agreeing to. “Please, honey, can you—”

“Faster?” Elliott fills in for him. “Harder?” He doesn’t even wait for Kurt’s answering nod before he starts to fuck into him faster, and harder. It took him a couple of times to learn that he can be basically how rough he wants with Kurt, and that Kurt will still  _love_  it. Now Elliott trusts him completely to let him know if it’s too much, so he just goes for it, fucking Kurt relentlessly, driving them both towards the edge. When he feels himself getting close, he reaches down and rubs Kurt’s clit, tries to keep it slow at first, not matching the pace of his thrusts at all, but he gives that up after just a few seconds and rubs hard and fast on Kurt’s clit, too, 

“ _Yes_ ,” Kurt moans, arching his back again and writhing in the air. The skirt has twisted, the zipper from the back is on the front of Kurt’s hip, the shirt is untucked, and Elliott can feel that one of the stockings have slid down. Elliott slows down the pace of his thrusts a little, but keeps rubbing Kurt’s clit. He tries to take it all in, the vision of Kurt dishevelled in these clothes, twisting in pleasure on their bed, he wants to save this and jerk off to it for the rest of his life. 

Kurt doesn’t agree with that plan, though, he whines when Elliott slows down and uses his heel to push him again, making him speed up and add more force. “Yes,” he moans again. “Yes, yes, come on,  _yes_.” His pussy clenches around Elliott’s cock, and it only takes a couple of more thrusts before Elliott is coming too, spilling into Kurt. 

They’re both panting hard when Elliott lies down beside Kurt, but he still can’t resist to reach down and drag his fingers between Kurt’s pussy lips, getting them sticky with come, and pushing it back into Kurt. 

“Mmm, no,” Kurt says, trying to twist away, but not making too much of an effort. 

“Later?” Elliott asks, sucking the come off of his fingers before kissing Kurt, who lets out a pleased moan and licks into his mouth, trying to chase the taste of them mixed together. 

“Later,” he agrees. “When you’ve gotten me out of these clothes.” He pulls at his shirt and frowns, it’s started to stick to his skin in places where he’s been sweating, and it’s wrinkled all over. 

“Hmm, I’m not sure I  _want_  you out of these clothes,” Elliott says, stroking over Kurt’s hip and smoothing out the skirt. 

Kurt rolls his eyes. “I’ll put them on again,” he sighs, acting as if it’s a big sacrifice, as if he doesn’t get at least as turned on as Elliott by it. 

“You promise?” Elliott says, nosing at Kurt’s throat and up his cheek, until he can kiss his mouth. 

“I promise,” Kurt says, smiling at him. “This was hot.”

“Yes,” Elliott agrees, “yes it was.”


End file.
